Potassium borohydride → 6-(1,3-Dioxolan-2-yl)-α-methyl-2-pyridinemethanol

HRID 376296Notes

Reaction equation

HRID 376296 reaction equation
[BH4-].[K+].[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[C:8]1[N:13]=[C:12]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:10][CH:9]=1>CO>[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[C:8]1[N:13]=[C:12]([CH:14]([OH:16])[CH3:15])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 4192641Potassium borohydrideHCID 10511974HCID 10511974, compound

Product 1

HCID 193617486-(1,3-Dioxolan-2-yl)-α-methyl-2-pyridinemethanolYield 76.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.50 g of potassium borohydride (9.27 mmol) is added in portions to a solution of 0.90 g of 1-(6-[1,3]dioxolan-2-yl-pyridin-2-yl)ethanone (4.66 mmol) in 15 ml of methanol. The mixture is stirred for 12 hours at room temperature and then methanol is evaporated off and the residue is taken up in chloroform. The organic phase is washed with water and then dried over sodium sulfate, filtered, and concentrated under vacuum. 0.70 g of a pale yellow oil is obtained, which oil is used in the next stage without further purification. 1H NMR (CDCl3) δ: 1.47 (d, 3H); 1.84 (s, 1H(exchangeable)); 4.11 (m, 4H); 4.88 (m, 1H); 5.82 (s, 1H); 7.25 (d, 1H); 7.41 (d, 1H); 7.75 (t, 1H).

Workup

  1. custommethanol is evaporated off
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-32d7a3d6ec7e48c5aa697681adb3f61d
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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